DE1098126B - Process for the production of colored condensation products - Google Patents

Description

GERMAN

The invention relates to a process for the production of new, colored condensation products, which are in particular suitable for pigmenting polyplasts and lacquers and which are characterized by their color strength, their heat resistance, characterized by their lightfastness and the fastness to sublimation of the colored polyplasts produced with them. It is known that by condensation of 3-iminoisoindol-1-one, of 3-thioisoindol-1-one or of 3-iminoisoindol-1-thione and their derivatives substituted on the benzo group with aromatic amines and hydrazines, which in addition to the amino group or the hydrazino group, another amino or hydrazino group, a substituted amino or hydrazino group or another directly connected or fused ring contain colored condensation products which are used to dye cellulose-containing! Material like Paper, for coloring lacquers and for pigmenting polyplasts are suitable. The known procedure proceeds with elimination of the 3-position substituent in the form of ammonia or hydrogen sulfide Heating the components alone or in inert organic solvents or diluents such as glacial acetic acid or alcohols, with the formation of a C = N double bond between the amine nitrogen atom and the 3-position carbon atom of the isoindole ring. Condensation products in the benzo radical of the isoindole ring contain more than two substituents, but have not become known by this process. The present patent is a process for the production of colored condensation products by condensation of a polyprimary Amino compound with the amount equivalent to the amino groups of the same or different isoindol-1-ones, which contain easily exchangeable substituents in the 3-position which have two bonds according to type or number stress and are more mobile than double-bonded oxygen or corresponding isoindolenines with simultaneous hydrolysis, characterized in that such isoindol-1-ones or isoindolenines are used, which are tetrahalogenated in the benzene residue.

The isoindoion derivatives used according to the invention contain, by definition, four halogen substituents in the benzene ring, like chlorine, bromine or fluorine. The tetrachloride compounds are particularly important from a technical point of view. as Easily mobile substituents can be in the 3-position of the isoindol-1-one compounds used according to the invention for example the imino group = NH, organically substituted imino groups = N - R, where R an alkyl, aralkyl, cycloalkyl or an iso- or heterocyclic aryl radical, for example the methyl, Ethyl, butyl, hydroxyethyl, benzyl, cyclohexyl, phenyl, methylphenyl, chlorophenyl or 2-pyridyl group, means a doubly bonded sulfur atom, two halogens, two secondary amino groups or two

Method of manufacture
of colored condensation products

Applicant:
JR Geigy AG, Basel (Switzerland)

Representative: Dr. F. Zumstein
and Dipl.-Chem. Dr. rer. nat. E. Assmann,
Patent Attorneys, Munich 2, Bräuhausstr. 4th

Claimed priority:
Switzerland from July 13, 1956

Dr. Andre Pugin, Basel (Switzerland),
has been named as the inventor

Ether groups such as alkoxy and alkyl mercapto groups may be present. These are tetrahalogen-substituted in the benzo radical Isoindoion derivatives are new. The 3-imino compounds are obtained, for example, from tetrahalophthalic anhydride when heated in nitrobenzene with urea and ammonium molybdate. But let the purity 3-Iminoisoindol-l-one thus represented is very close to be desired. Reactive ones that are purer and therefore more suitable in the process according to the invention Isoindoion compounds are obtained by a new method from those tetrahalogenated on the benzene ring Phthalimides by the action of at least 1 mol of phosphorus pentachloride with exclusion of moisture in inert organic solvents at elevated temperature. This produces 3,3-dichloroisoindol-l-ones, which you either use it directly or first with ammonia or primary organic amines in the likewise can convert very reactive corresponding 3-imino compounds. You can also use the known 1,3,3-trichloroisoindolenines tetrahalogenated in the benzo radical go out, which from the corresponding phthalimides when exposed to 2 mol Phosphorus pentachloride is formed in the heat with the exclusion of moisture, and these 1,3,3-Trichlorisoindolenine before or during the reaction with amines, expediently using hydrous organic Solvents, carefully in the cold or at a slightly elevated temperature to the corresponding 3,3-dichloroisoindol-1-ones hydrolyze. In practice, 1 mol of tetrachlorophthalimide is used with 1.1 to 1.3 mol of phosphorus pentachloride around and used the 3,3-dichloroisoindol-l-on-one which crystallizes out on cooling, filtered off

109 507/452

1 090126

³ 4

binding. But you can also use the reaction solution directly magnesium oxide or calcium carbonate. Organic too

use when due to the presence of moist nitrogen bases can optionally be used

speed before or during the conversion with the amino, for example pyridine, quinoline or dialkylanilines.

compounds for the hydrolysis of the resulting colored condensate according to the invention

1,3,3-Trichlorisoindolenine provides. 5 are sation products insofar as they are compounds

It is very difficult to produce those obtainable according to the invention without acidic, salt-forming groups

Colored condensation products are, for example, soluble bodies. You divorce yourself from solving the

The following polyprimary amino compounds can be used: Components already in the heat and can through

Hydrazine and preferably aromatic polyprimary filtering off and washing with organic solvents

Amino compounds of the iso- or heterocyclic series, io agents, water, aqueous alkalis and aqueous

for example 1,3- and 1,4-diaminobenzenes, 4,4'-diamino acids are easily purified. If starting materials

diphenyl and triphenylalkanes, 4,4 ', 4 "-Triaminotri- are used, which contain acidic, salt-forming groups,

phenylmethane, 4,4-diaminodiphenylamines, 4,4'-di- for example sulfonic acid or carboxyl groups,

ammodiphenyle ^^ - Diaminoterphenyle ^^^ '- Triamino- hold, one works expediently in organic-aqueous

diphenyls, 4,4'-diaminostilbenes, 1,4-, 1,5-, 1,7- and 15 solution. Depending on the polyamine used

2,6-diaminonaphthalenes, 2,7-diaminofluorene, 1,4- and yellow, orange, red, brown, violet to black condensate

1,5-diaminoanthraquinones, 2,6-diaminopyridines, 2,7-di- sation products are obtained. If they are insoluble in water,

aminocarbazole, 2- (4'-aminophenyl) -6-aminobenzthiazole, they represent thanks to their excellent lightfastness, their

2,6-diaminobenzothiazole, 2,5-bis- (4-aminophenyl) -oxdia- color strength and fastness to migration in polyplasts, such as

zoles and thiadiazoles. You can of course also use iso- and polyvinyl chloride, very valuable pigment dyes,

Use heterocyclic-aromatic polyamines, which are used for pigmenting paints, polymeric

which the amino groups in other positions plastics and rubber are excellent. she

to take. Preferably, however, diaminover can also be used in finely divided form for dyeing

bonds in which the amino groups take the positions of paper or for dyeing viscose or cellulose

possible to take quinones. All aromatic rings 25 esters or polyamides are used in the spinning pulp

can be further substituted, for example by. Provided they are water-solubilizing, salt-forming

Alkyl groups, such as methyl, ethyl, tert-butyl, tert-groups, you can either with the for

Amyl groups, through ether groups such as methoxy, alkaline earth, earth or heavy

Convert ethoxy, butoxy, phenoxy, methyl mercapto, ethyl metal salts into insoluble colored lacquers or ever

mercapto, phenyl mercapto groups, by halogen 30 according to affinity for dyeing cellulosic! Material,

atoms, through sulfonic acid and carboxylic acid groups, such as paper, of cellulose fibers or animal fibers

their salts, esters and amides, through nitro, acylamino, use.

secondary and tertiary amino groups. In comparison with the l-phenylamino-3-phenylimino condensation products known from the German patent for the color strength of the font 906935 available according to the invention, the selection of such 4,5,6,7-tetrachloroisoindolenine has the diprimary amino compounds according to the invention, which a system of conjugated chlorisoindol-1-one and 1,4-diaminobenzene give better double bonds for the available condensation product from 3,3,4,5,6,7-hexa linkage of the isoindoion rings. Examples of such diamino overcoating fastness, and compared to the compounds are the hydrazine, diel, 4-diaminobenzene, USA.-Patent 2537352 known condensation, 4 ^r -diaminodiphenyl and 4,4'-diaminostilbene compound 40 product from dichloro 3-iminophthalimide and benzidine fertilize as well as the diamino compounds of higher isocyc- shows the comparable according to the invention obtainable lischer or heterocyclic condensed structures, condensation product of 3,3,4,5,6,7-hexachloroisoindolvorin the amino groups the positions of possible 1-one and benzidine a better one Lightfastness.
Take quinones. The above list contains some The following examples illustrate the invention. Examples of such diamino compounds. In technical terms, the parts, unless otherwise expressly of interest, mean the 1,3- and 1,4-diaminobenzene-, which is noted on loan, parts by weight. The temperatures are 4,4'-diaminodiphenyl, 4,4'-diaminostilbene and those in degrees Celsius.
Quinones corresponding diaminonaphthylene derivatives

linge, also the derivatives of 4,4'-diaminodiphenyl- Example 1

compounds formed by ring-forming links 50 To a solution of 34 parts 3,3,4,5,6,7-hexachloro

to fluorene, diphenyloxides, diphenylene sulfides, di-isoindol-1-one in 300 parts of o-dichlorobenzene is one

phenylene sulfones, carbazoles are further condensed. For dissolving 5.4 parts of 1,4-diaminobenzene in 200 parts

All of these compounds are considered to be added to the aromatic o-dichlorobenzene. The yellow one that emerged immediately

Rings can be further substituted. The suspension is heated to 160 to 170 ° for 3 hours.

The condensation of these polyprimary amino compounds is then filtered hot and the precipitate with o-di-

Applications washed with the 3-reactive substi- chlorobenzene, alcohol and acetone. You get

tuated isoindol-1-ones runs very smoothly, often already 32 parts of a pure, strongly colored orange-yellow pigment,

in the cold, possibly while warming the intimately which is characterized by excellent light, migration and

mixed components, particularly advantageous in terms of solvent fastness.

Presence of inert organic solution and Ver 60 The 3,3,4,5,6,7-Hexachlorisoindol-l-one is through

thinners, such as hydrocarbons, 1 mole of tetrachlorophthalimide is heated for 1 hour with halogen

hydrocarbons, aliphatic or alicyclic 1.2 moles of phosphorus pentachloride in chlorobenzene at 125 °

Ethers and ketones or esters. Manufactured as an inert solution. Unchanged is first filtered while hot

medium can, for example, cyclohexane, benzene, toluene, tetrachlorophthahmid, with the new one when it cools down

Xylenes, 1,2,3,4-tetrahydronaphthalene, naphthalene, di-65 hexachloroindolone crystallized out. It continues to melt

phenyl, carbon tetrachloride, tetrachlorethylene, chlorine recrystallization from benzene with decomposition

benzene, di- and trichlorobenzene, nitrobenzene, dibutyl-205 to 206 °.
ether, dioxane, diphenyl ether, acetone, cyclohexanone

be used. If necessary, one works in Calculated for C ₈ HONCl ₆ N = 4.11%;

Presence of acid-binding agents, such as sodium acetate, 70 found N = 4.27 ° / ₀ ..

5 6

If 10 parts of this pigment, 10 parts of alumina, 67 parts of polyvinyl chloride, 33 parts of dioctyl

hydrate, 30 parts medium viscosity linseed oil varnish and phthalate, 2 parts dibutyltin dilaurate, 1 part of the above

0.2 parts of cobalt linoleate mixed pigment and 2.5 parts of titanium dioxide on a three-roll mill for 15 minutes

and rubbed, a graphic color can be obtained at 150 ° on a roller mill and mixed into one

which reddish-yellow prints are processed from special pure 5 thin film, then their red is distinguished

unity and color strength as well as of excellent solution coloring due to good color strength and excellent

results in medium, acid, alkali and light fastness. Heat, migration and light fastness.

Yellow pigments of similar good properties

is obtained when in this example the 1,4-diamino. Example 5

benzene by 7.4 parts of 1,4-diaminonaphthalene or by ίο A solution of 10.6 parts of 4,4'-diamino-3,3'-di-

10.6 parts of 4,4'-diaminoazobenzene replaced. methyldiphenyl in 150 parts of o-dichlorobenzene

An even redder pigment of equally good properties together with a solution of 35 parts 3,3,4,5,6,7-

Properties are obtained if, in this example, the hexachloroisoindol-1-one in 500 parts of o-dichlorobenzene

1,4-Diaminobenzene heated by 12.15 parts of 3,3'-dichlorobenzidine for 3 hours to 160 to 170 ° with stirring,

replaced. Pigments of a greener hue and from 15 Man filtered off hot, the precipitate was washed with

very good fastness properties are also obtained when in alcohol and acetone and obtained after drying

in this example the 1,4-diaminobenzene by 5.4 parts 34 parts of a pure red pigment of very good quality

1,3-diaminobenzene, 6.1 parts of l-methyl-2,6-diaminobenzene, oil, acid, alkali, solvent, migration and

12.3 parts of 2,7-diamino-dibenzothiophene-l, l-dioxide or light fastness.

Replaced 11.5 parts of 4,4'-diamino-3-nitrodiphenyl. 20 Red pigments of equally good quality are also obtained

Properties if you put in this example

Example 2 _of 4 ₎ 4'_Diamino-3,3'-dimethyldiphenyl 7.4 parts of 1,5-di-

To a solution of 6.8 parts of 3,3,4,5,6,7-hexachloraminonaphthalene or 10.5 parts of 4,4'-diaminostilbene

isoindol-1-one in 200 parts of benzene, a cold solution is used.

of 1.84 parts of 4,4'-diaminodiphenyl in 200 parts of Example 6
Benzene added. An orange color appears immediately

Precipitation. The mixture is stirred for a further 1 hour at space 14.2 parts of S-Iminc ^ S.o ^ -tetrachloroisoindol-l-one and temperature, the pigment is filtered off and washed with 4.6 parts of 4,4'-diaminodiphenyl in 300 parts Benzene, acetone and water. The pure orange glacial acetic acid was refluxed for 2 hours. It educates Pigment can be recrystallized from a lot of nitrobenzene and becomes a pure orange pigment that melts over 360 °. It possesses excellent light-filtered properties and by washing with glacial acetic acid, alcohol and authenticity as well as a very good migration, solvent, acetone is cleaned. The pigment is identical to Overcoating, oil, acid and alkali fastness. that of example 2.

Are z. B. 10 parts of this pigment, 10 parts The S-Imino ^ S.o ^ -tetrachloroiso-

Titanium dioxide, 35 parts of a 60% solution of a modi- 35 indol-1-one is obtained by reacting 34 parts

ficated urea alkyd resin in xylene-butanol (1: 1), 3,3,4,5,6,7-hexachloroisoindol-1-one with 60 parts of aq.

10 parts of turpentine oil and 5 parts of xylene in spherical ammonia. It's a pale yellow powder

Mill ground for 45 hours, so can after pouring which melts at 320 ° with decomposition. You get

on aluminum foils and baked for 1 hour with the same pure orange pigment when you are in

120 ° a pure orange color of excellent 40 this example with 4.6 parts of 4,4'-diaminodiphenyl

Fastness properties, in particular of very good overcoating instead of 3-imino-4,5,6,7-tetrachloroisoindpl-l-one, 18 parts

authenticity, to be preserved. S-Phenylimino ^ .S.o ^ -tetrachlorisoindol-l-one (F. 264 bis

. . 265 °). The S-phenylimino ^ .S.o ^ -tetrachlor-

Example 3 isoindol-1-one is obtained by reacting 34 parts

6.6 parts of S ^ '- dichloro ^^' - diaminodiphenyl chlorohydrate 45 3,3,4,5,6,7-Hexachlorisoindol-l-one with 40 parts of aniline

are with 11.6 parts of S-Imino ^ S.o ^ -tetrachloroisoindole- in benzene at 70 °.

1-one in 200 parts of nitrobenzene ¹ _{l for 2} hours at 200 ° If in this example the 3-imino-4,5,6,7-

heated. The resulting yellow-brown pigment is hot tetrachloiisoindol-1-one by 18 parts of the 3- (2'-pyridyI-

filtered off from the nitrobenzyl, with alcohol, water and imino) -4,5,6,7-tetrachlorisoindol-l-one (F. 264 to 266 °),

Acetone washed. It has good migration and 50 manufactured from 3,3,4,5,6,7-tetrachlorisoindol-l-one and

Lightfastness. The 3-imino-4,5,6,7-tetrachloroisoindol-1-one 2-aminopyridine in o-dichlorobenzene is replaced, so obtained

1 mole of tetrachlorophthalic anhydride and 4 moles are used to make the same orange pigment.

Urea in the presence of ¹ Z ₁₀₀ moles of ammonium. .

molybdate in nitrobenzene by heating to 140 ° - Example 7

posed. The reaction product, which is not entirely pure, melts 6.6 parts of 1,3,3,4,5,6,7-heptachloroisoindolenine

with decomposition to about 305 °; it provides a high quality, dissolved in 80 parts of dioxane and made into a solution of

but not very pure pigment. 2 parts of 4,4-diaminodiphenyl chlorohydrate in 300 parts

. Water added. The suspension is heated to 80 °,

Example 4 _the orange colored pigment filtered off and with alcohol

Washed a solution of 6.8 parts of 3,3,4,5,6,7-hexachloro-60 and acetone. It can be converted from nitrobenzene

isoindol-1-one in 100 parts of xylene will be crystallized together with and is then identical to the im

a solution of 2.44 parts of 4,4'-diamino-3,3'-di- Example 2 prepared pigment,

methoxydiphenyl in 100 parts of xylene for 2 hours. "

heated to reflux. The pigment is filtered off and Example 8

washed with alcohol. It is a yellowish red 65 6.8 parts of 3,3,4,5,6,7-Hexachlorisoindol-l-one are in

pigment with very good fastness properties. When this pigment is dissolved in 100 parts of acetone and added to 3.7 parts of 4,4'-di-

again in 100 parts of nitrobenzene for 1 hour on aminostilbene-2,2'-disulfonic acid, dissolved as the sodium salt,

200 ° is heated, it is bluish-tinted red, and its added in 200 parts of water at room temperature,

very good lightfastness is still noticeable The resulting orange-colored precipitate is filtered off,

improved. 70 washed with water and dried. The dye

7 8

dissolves with a yellow color in aqueous alkalis and benzene is added and the color continues for 2 hours at 125 ° Orange-yellow paper. touched. 300 parts are added to the suspension

If you use the 4,4-T) ianunostüben ethanol in this example, filter off and wash the pigment with alcohol, 2,2'-disulfonic acid with 3 parts of 3,3'-dicarboxy acetone, dilute ammonia solution and water and 4,4'-diaminoazobenzene replaced, you get a 5 dries it. This raw pigment is again through brown, water-soluble dye. Boil cleaned with nitrobenzene and hot filtration.

. . ■ ■ The pigment is orange and has a good color

Example 9 Migration and Lightfastness.

3.4 parts of 3,3,4,5,6,7-Hexachlorisoindol-l-one are with. _Ä

Dissolve 1 part hydrazine hydrate in 100 parts for 5 minutes

Chlorobenzene heated to 100 °. The precipitated greenish 17.2 parts of 3,3,4,5,6,7-Hexachlorisoindol-l-one are

yellow pigment is nitrated hot and dissolved with acetone and in 250 parts of benzene and with a solution of Water washed. It is characterized by its purity 4.6 parts of 4,4'-diaminodiphenyl in 200 parts of benzene and its excellent migration and lightfastness and 8 parts pyridine mixed and 1 hour on the back out. 15 nut heated. An orange-colored, pure one forms Example 10 pigment, which is sucked off and mixed with alcohol and water

is washed.

6.8 parts of 3,3,4,5,6,7-Hexachlorisoindol-l-one are used in this example instead of pyridine

100 parts of dioxane are mixed with 1.58 parts of pyridine. Use 10.1 parts of triethylamine,
a white precipitate immediately appears. To do this, an ao

Solution of 1.84 parts of 4,4'-diaminodiphenylin 50 parts Example 17

Dioxane was added, the suspension being yellow at first, 4.41 parts of S.S-bis-morpholino ^ .S.oJ-tetrachlor-

then turns orange. After 2 hours of heating on isoindol-1-one (mp 211-212 °), produced by Um-90 The orange pigment is filtered off up to 95 °. and washed with alcohol and water. It has a 25 pholine in benzene, with 0.92 parts of 4,4'-diamino being excellent Lightfastness. diphenyl in 50 parts of glacial acetic acid heated to 100 ° for 5 minutes.

. - ^ ₁₁ After filtering off and washing with glacial acetic acid and water

.Example 11 is an orange pigment of excellent

Isolated from a solution of 13.2 parts of 3,3,4,5,6,7-hexa fastness properties.

chlorisoindol-1-one in 200 parts of o-dichlorobenzene is 30 An orange-colored pigment similar to a solution of a mixture of 1.84 parts of 4,4'-diamino-good properties is obtained if in this example the diphenyl and 2.53 parts of 3 , 3'-Dichlorobenzidine in 100 parts of 3,3-bis-morphonno-4,5,6,7-tetracUorisomdol-l-one was added by o-dichlorobenzene. The resulting orange-5.25 parts of 3,3-bis- & butylamino-4,5,6,7-tetrachloro-colored suspension is heated to 170 ° for 1 hour, isoindol-1-one, prepared by reacting the 3,3, 4,5,6, the precipitate filtered off and washed with acetone. 35 7-Hexachlorisoindol-l-one with di-n-butylamine in benzene, The pigment obtained in this way is more yellow, but has been replaced immediately,
good fastness properties like that of example 2. Example 18

EXAMPLE 12 _{331 parts of} s ^ .Dimethoxy- ^ S ^ J-tetrachloriso-2.38 parts of 1,5-diaminoanthraquinone are prepared in 100 parts of indol-1-one (melting point 165 ° to 175 ° with decomposition)

len hot nitrobenzene and dissolved, with 6.6 parts 3,3,4,5, from 3,3,4,5,6,7-Hexachlorisoindol-l-one and. Sodium-

6,7-Hexachlorisoindol-l-one dissolved in 100 parts of nitro methylate in methyl alcohol, with 0.54 parts

benzene condensed for 2 hours at 140 °. The ab-1,4-diaminobenzene in 50 parts of o-dichlorobenzene for 2 hours

filtered pigment is then heated again for 1 hour at 150 °. A yellow pigment of

100 parts of nitrobenzene stirred at 200 °, filtered off while hot 45 very good fastness properties,

and washed with alcohol and acetone. The ._. . _Q

Pigment is blue-black and is characterized by its .Example, y

good fastness properties and its color strength. 3.59 parts of S.S-diethoxy ^ .S.ö ^ -tetrachlorisoindole-

1-one (m.p. 175 to 180 ° with decomposition), made from

Example 1.5 _5o 3 ^ 4 ^ 6,7-hexachloroisoindol-1-one and sodium ethylate

13 parts of 3,3,4,5,6,7-Hexachlorisoindol-l-one are to- in ethyl alcohol, with 0.92 parts of 4,4'-diaminodi-

together with 2.2 parts of 2,6-diaminopyridine in 200 parts of phenyl in 50 parts of glacial acetic acid for 30 minutes to the boil

o-Dichlorobenzene heated to 170 ° for 2 hours. That heats up. An orange pigment of

yellow pigment is filtered off hot and with alcohol excellent fastness properties,

washed. It possesses good acid, alkali, oil and 55 _. . . _ "

Lightfastness. Example 20

Example 14 Parts of 2,5-bis- (4'-aminophenyl) -oxdiazole become

with 6.8 parts of 3,3,4,5,6,7-Hexachlorisoindol-l-one in

10 parts of 3,3,4,5,6,7-Hexachlorisoindol-l-one are in 100 parts of o-dichlorobenzene for 2 hours under a 150 parts of o-dichlorobenzene dissolved and heated to 120 ° with a solution 60 vacuum of 90 mm Hg. After this of 2 parts of 2,4,4'-triaminodiphenyl in 100 parts of filtering off and washing with alcohol, acetone and Mixed o-dichlorobenzene and heated to 150 ° water for 2 hours, a pure yellow pigment is obtained. The result is a reddish-yellow pigment with excellent light and migration fastness properties. Used Fastnesses. one in place of the 2,5-bis (4'-aminophenyl) oxdiazole _. .65 3.20 parts of 2,5-bis- (3'-methyl-4'-aminophenyl) -oxdiazole, Example Io this is how you get a redder pigment of similar good quality In 500 parts of chlorobenzene, 142.5 parts are tetra properties.

chlorphthalimide with 110 parts of phosphorus pentachloride pigments of even redder shades are obtained,

Heated to 125 ° for 1 hour. Then a solution is obtained if, in this example, the 2,5-bis- (4'-aminophenyl) -

of 48 parts of 4,4'-diaminodiphenyl in 300 parts of chlorine-70 oxdiazole by 3.12 parts of 2,5-bis- (4'-aminophenyl) -

thiodiazole or 3.8 parts of 2,5-bis- (3'-chloro-4'-aminophenyl) -thiodiazole replaced.

Claims (7)

PATENT CLAIMS: 1. A process for the preparation of colored condensation products by condensation of a polyprimary amino compound with the amount equivalent to the amino groups of the same or different isoindol-1-ones which contain easily interchangeable substituents in the 3-position which claim two bonds according to type or number and are more mobile than the doubly bonded oxygen or corresponding isoindolenines with simultaneous hydrolysis, characterized in that such isoindol-1-ones or isoindolenines are used which are tetrahalogenated in the benzene radical. 2. The method according to claim 1, characterized by the use of diprimary amino compounds the iso- or heterocyclic-aromatic so series. 3. The method according to claims 1 and 2, characterized by the use of such diprimary Amino compounds which are involved in linking the more highly halogenated isoindol-1-one rings Form a system of conjugated double bonds. 4. Process according to claims 1 to 3, characterized by the use of diprimary Amino compounds of the benzene, diphenyl, stilbene and naphthalene series. 5. Process according to claims 1 and 3, characterized by the use of hydrazine as a diprimary amino compound. 6. The method according to claims 1 to 5, characterized by the use of such isoindol-1-ones, the 3-position imino, which can be organically substituted, two halogens, contain two secondary amino groups or two alkoxy groups. 7. The method according to claims 1 to 6, characterized by the use of 3,3,4,5,6,7-hexachloroisoindole-1 -on. Considered publications:
German Patent No. 906 935;
U.S. Patent No. 2,537,352. When the announcement was made, two Eärbe boards were laid out. © 109 507/452 1.